2-[(2S,3R,5R)-5-((4S,5R)-5-Isopropenyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-methyl-tetrahydro-furan-2-yl]-ethanol | 537007-66-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(2S,3R,5R)-5-((4S,5R)-5-Isopropenyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-methyl-tetrahydro-furan-2-yl]-ethanol
• 英文别名: 2-[(2S,3R,5R)-5-[(4S,5R)-2,2-dimethyl-5-prop-1-en-2-yl-1,3-dioxolan-4-yl]-3-methyloxolan-2-yl]ethanol
• CAS: 537007-66-2
• 化学式: C₁₅H₂₆O₄
• 分子量: 270.369
• InChiKey: IEAZSXFLPNCVDI-ITGHMWBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(2S,3R,5R)-5-((4S,5R)-5-Isopropenyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-methyl-tetrahydro-furan-2-yl]-ethanol 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 pyridine-SO3 complex 、 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 8.0h， 生成 methyl {(2S,3R,5R)-5-[(1R,2R)-1,2-dihydroxy-3-methyl-3-butenyl]-3-methyltetrahydrofuran-2-yl}-acetate
  参考文献：
  名称：

  Absolute stereochemistry of amphidinolide C: synthesis of C-1–C-10 and C-17–C-29 segments

  摘要：

  Two of each diastereomers of the C-1-C-10 and C-17-C-29 segments of amphidinolide C (1) were synthesized. Comparing the H-1 NMR chemical shifts of its MTPA esters with those of linear methyl ester of 1, the absolute configurations at C-7, C-8, C-20, C-23, and C-24 in amphidinolide C (1) were confirmed to be all R. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00142-x
• 作为产物：
  描述：

  (1R,2R)-1-{(2R,4R,5S)-5-[2-(tert-butyldimethylsilyloxy)ethyl]-4-methyltetrahydrofuran-2-yl}-3-methyl-1-triethylsilyloxy-3-buten-2-ol 在 4-甲基苯磺酸吡啶 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 7.0h， 生成 2-[(2S,3R,5R)-5-((4S,5R)-5-Isopropenyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-methyl-tetrahydro-furan-2-yl]-ethanol
  参考文献：
  名称：

  Absolute stereochemistry of amphidinolide C: synthesis of C-1–C-10 and C-17–C-29 segments

  摘要：

  Two of each diastereomers of the C-1-C-10 and C-17-C-29 segments of amphidinolide C (1) were synthesized. Comparing the H-1 NMR chemical shifts of its MTPA esters with those of linear methyl ester of 1, the absolute configurations at C-7, C-8, C-20, C-23, and C-24 in amphidinolide C (1) were confirmed to be all R. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00142-x

文献信息

• Absolute stereochemistry of amphidinolide C: synthesis of C-1–C-10 and C-17–C-29 segments
  作者：Takaaki Kubota、Masashi Tsuda、Jun'ichi Kobayashi

  DOI：10.1016/s0040-4020(03)00142-x

  日期：2003.3

  Two of each diastereomers of the C-1-C-10 and C-17-C-29 segments of amphidinolide C (1) were synthesized. Comparing the H-1 NMR chemical shifts of its MTPA esters with those of linear methyl ester of 1, the absolute configurations at C-7, C-8, C-20, C-23, and C-24 in amphidinolide C (1) were confirmed to be all R. (C) 2003 Elsevier Science Ltd. All rights reserved.